Norpipanone

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Norpipanone
Norpipanone2DCSD.svg
Clinical data
Other namesHerchst 10495, NIH-7557
ATC code
  • None
Legal status
Legal status
Identifiers
  • 4,4-diphenyl-6-(1-piperidinyl)-3-hexanone
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard 100.008.383 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C23H29NO
Molar mass 335.491 g·mol−1
3D model (JSmol)
  • O=C(C(c1ccccc1)(c2ccccc2)CCN3CCCCC3)CC
  • InChI=1S/C23H29NO/c1-2-22(25)23(20-12-6-3-7-13-20,21-14-8-4-9-15-21)16-19-24-17-10-5-11-18-24/h3-4,6-9,12-15H,2,5,10-11,16-19H2,1H3
  • Key:WCDSHELZWCOTMI-UHFFFAOYSA-N

Norpipanone (INN, BAN; Hexalgon) is an opioid analgesic related to methadone which was developed in Germany and distributed in Hungary, Argentina, and other countries. [2] [3] It had originally not been under international control but upon observation of case reports of addiction it was reviewed and shortly thereafter became a controlled substance. [2] [3] In the United States, it is a Schedule I controlled substance (ACSCN 9636, zero annual manufacturing quota as of 2014). The salts in use are the hydrobromide (free base conversion ratio 0.806) and hydrochloride (0.902).

Contents

Synthesis

Norpipanone synthesis: Norpipanone synthesis.png
Norpipanone synthesis:

See also

Related Research Articles

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Dipipanone, sold under the brand names of Pipadone and Diconal is a strong opioid analgesic drug, used for acute pain by mouth (PO) for adults. It is often used in instances where morphine is indicated but cannot be used due to the patient being allergic to morphine. In analgesic potency 25 mg dipipanone is approximately equivalent to 10 mg morphine.

<span class="mw-page-title-main">Dextromoramide</span> Opioid analgesic drug

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<span class="mw-page-title-main">Levorphanol</span> Opioid analgesic drug

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<span class="mw-page-title-main">Levomethorphan</span> Opioid analgesic

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<span class="mw-page-title-main">Methorphan</span> Group of stereoisomers

Methorphan comes in two isomeric forms, each with differing pharmacology and effects:

<span class="mw-page-title-main">Piritramide</span> Synthetic opioid

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<span class="mw-page-title-main">Properidine</span> Chemical compound

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<span class="mw-page-title-main">Hydroxypethidine</span> Chemical compound

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<span class="mw-page-title-main">Phenampromide</span> Chemical compound

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<span class="mw-page-title-main">Proheptazine</span> Opioid analgesic drug

Proheptazine is an opioid analgesic related to pethidine. It was invented in the 1960s.

<span class="mw-page-title-main">Benzethidine</span> Chemical compound

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<span class="mw-page-title-main">Furethidine</span> Chemical compound

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<span class="mw-page-title-main">Acetylmethadol</span> Synthetic opioid analgesic

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<span class="mw-page-title-main">Alphamethadol</span> Synthetic opioid analgesic drug

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<span class="mw-page-title-main">Normorphine</span> Chemical compound

Normorphine is an opiate analogue, the N-demethylated derivative of morphine, that was first described in the 1950s when a large group of N-substituted morphine analogues were characterized for activity. The compound has relatively little opioid activity in its own right, but is a useful intermediate which can be used to produce both opioid antagonists such as nalorphine, and also potent opioid agonists such as N-phenethylnormorphine. with its formation from morphine catalyzed by the liver enzymes CYP3A4 and CYP2C8.

<span class="mw-page-title-main">Methyldesorphine</span> Chemical compound

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<span class="mw-page-title-main">Isomethadone</span> Opioid analgesic and cough suppressant drug

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<span class="mw-page-title-main">Alphacetylmethadol</span> Synthetic opioid analgesic drug

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<span class="mw-page-title-main">Noracymethadol</span> Chemical compound

Noracymethadol (INN) is a synthetic opioid analgesic related to methadone that was never marketed. In a clinical trial of postpartum patients it was reported to produce analgesia comparable to that of morphine but with less nausea, dizziness, and drowsiness. Other side effects included salivation, ataxia, and respiratory depression that was reversible by naloxone. Similarly to many of its analogues, noracymethadol is a Schedule I controlled substance in the United States with an ACSCN of 9633 and 2013 annual manufacturing quota of 12 grammes. and is also controlled internationally under the United Nations Single Convention on Narcotic Drugs of 1961. The salts known are the gluconate and hydrochloride (0.903).

References

  1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. 1 2 Buckingham JB (December 1995). Dictionary of Organic Compounds. CRC Press. p. 2883. ISBN   978-0-412-54090-5 . Retrieved 11 May 2012.
  3. 1 2 Patterson DS (12 March 2002). Foreign Relations of the United States, 1961-1963, Volume XXV: Organization of Foreign Policy; Information Policy; United Nations; Scientific Matters. Government Printing Office. pp. 766–767. ISBN   978-0-16-050885-1 . Retrieved 11 May 2012.
  4. Dupré DJ, Elks J, Hems BA, Speyer KN, Evans RM (1949). "113. Analgesics. Part I. Esters and ketones derived from α-amino-ω-cyano-ωωdiarylalkanes". Journal of the Chemical Society (Resumed). Chemical Society: 500–510. doi:10.1039/JR9490000500.
  5. Bockmühl M, Ehrhart G (1949). "Über eine neue Klasse von spasmolytisch und analgetisch wirkenden Verbindungen, I". Justus Liebigs Annalen der Chemie. 561: 52–86. doi:10.1002/jlac.19495610107.